That’s high praise when you’re hanging out at Four Times Square, the headquarters of our parent company, Condé Nast, and the home of fashion magazines like Vogue, GQ, and Glamour. When someone at the Condé Nast building compliments your clothes, you’ve gotten over a pretty high bar.

Chicago company Proper Suit is bringing a dash of technology to the tailoring world.

The garment in question was made to measure for me by a Chicago company called Proper Suit, which is bringing a dash of technology to the tailoring world. It’s not the same as a truly bespoke suit, where a master tailor cuts a pattern to your measurements, and then tweaks it over multiple fittings. Still, the result of Proper Suit’s process fits me better than anything else I’ve ever worn, and costs little more than an off-the-rack number.

The process starts with an appointment with one of the company’s tailors (Proper currently services New York, Chicago, San Francisco, Washington DC, Los Angeles, Atlanta, Seattle, and Portland, Oregon). Over the course of an hour-long appointment, you try on various samples, and then the tailor starts to tweak the measurements of these standard patterns. You can work together to tweak what you’re looking for, whether it’s an aggressive, fashion-forward silhouette, or something a little more conservative and classic.

I tried to go for an updated classic look, nothing too crazy, but fitted. Then we got to pick fabrics for the suit itself, the lining, the edging on pockets, the thread and stitching, the buttons. In the hands of an amateur, it’s likely a recipe for tackiness, but Max, my tailor, helped guide me.

All of the measurements and specs then go to the company’s facility in China (the company’s founders, McGregor J. Madden and Richard Hall, met working in China, where they developed relationships with apparel factories). The fabric is cut using AutoCAD and a laser cutting system — once they have the pattern right, it’s easy to cut perfect suits for you each time. In about a month, you’ll have the suit.

A strip of fabric sewn around the inside bottom of each pant leg serves as a shield against wear. Photo by Alex Washburn/Wired

There are lots of small details that really make the suit stand out for me. The waistband of the pants has a rubberized strip in it, to help keep your shirt tucked in. There’s a strip of fabric sewn around the inside bottom of each pant leg, which shields the main fabric from wear. There’s a special cell phone pocket sewn along a seam in the jacket, which keeps the phone from distorting the line of the coat.

The construction was excellent, both to my eye, and the eye of an independent tailor I asked to look at the suit. The fit was nearly perfect, although the cuffs were a hair long, and the jacket a touch large. After getting the suit, I talked to the Proper Suit team, and they tweaked my pattern, so the next suit should be right on.

All of this runs under $1,000 for standard fabrics, with more expensive fabric choices goosing the price up toward $2,000.

Madden and Hall aren’t stopping with suits; they’ve also launched a dress shirt service (called Hall & Madden) that delivers shirts made in the same factories as established fashion brands, at a rate of $150 for three shirts.

But really, while the quality to price ratio here is awesome, it’s compliments like those I got at work that will send me back to Proper Suit again soon.